The Millennial Career Crisis
There is an interesting tension appearing in the world at the moment, particularly amongst people in their 30s and 40s, although there are certainly some of us wandering into our 50s who are feeling it too.
It’s sometimes described as the Millennial Career Crisis. People who did what they were supposed to do, followed the prescription they were given, built the career, got qualified, worked hard and generally tried to construct the life they had been told would work, only to arrive somewhere around the middle and discover that it doesn’t quite look like they expected.
For some, it is falling apart. For others, it’s almost the opposite. They are discovering something in themselves again. They’re changing direction, questioning what they actually want, rediscovering interests and capabilities that disappeared somewhere along the way, becoming inspired and, in some cases, almost feeling refreshed or reborn.
Something has changed.
And I’m not sure it’s them.
What if the Millennial Career Crisis is actually another symptom of something we’ve been exploring throughout this whole rabbit hole?
The Industrial Age playbook doesn’t work the way it used to.
That’s interesting enough by itself. But for neuro-complex people, particularly those who have spent most of their lives without knowing they’re neuro-complex, there is another layer to this.
Because that feeling that the prescription doesn’t quite work?
Some of us have been living with that for most of our lives.
The prescription wasn’t stupid
I’ve been careful throughout these articles not to turn the Industrial Age into some sort of villain. It wasn’t. Nor were our parents stupid for giving us the advice they did.
The prescription made sense.
Go to school. Get educated. Get qualified. Find a career. Work hard. Meet somebody. Get married. Have some kids. Buy a house. Build some security. Keep progressing. Eventually retire.
It sounds almost quaint when you put the whole thing together like that, but it was a remarkably sensible approach to the world our parents understood. For many people it worked exceptionally well.
The boundaries around that world were also clearer. Work was work. Home was home. The hobby was the hobby. The club was the club. There was an increasing separation between the different parts of our lives, something I explored in the last article when we went looking for where all these supposedly new neurodivergent people had been hiding.
They hadn’t been hiding at all.
They were everywhere.
They were in families, workshops, sheds, art rooms, clubs, trades, technical departments and all sorts of places where the different parts of themselves had somewhere to exist.
The Industrial Age gave us compartments.
And the prescription we inherited was built around those compartments.
Then digital started knocking the walls down.
Eighteen jobs. Six careers.
I mentioned this towards the end of the last rabbit hole, and it’s worth coming back to because it is an extraordinary number when you stop and think about what it means.
Today’s school leavers are expected to have something like 18 jobs across six careers during their lifetime (McCrindle, 2024; Wodonga TAFE, 2024).
Six careers.
Not six employers doing essentially the same thing.
Six careers.
Compare that with the prescription many of us were given at school. What are you going to be when you grow up? Choose your subjects accordingly. Get the qualification. Enter the profession. Build your career.
We were essentially being asked to choose the road.
Now we’re telling people the road will probably disappear underneath them several times during their working lives.
That’s not simply a change in the employment market. It changes what we need from human beings.
The idea that you can go to university, become qualified, enter a job and then spend the next 40 years applying what you learnt doesn’t make much sense when the work itself keeps changing. Even when the profession remains the same, the way two organisations actually do that work can be completely different.
Different systems. Different people. Different customers. Different processes. Different technology. Different culture. Different expectations. Different ways of creating value. Different secret sauce of success.
The qualification might get you through the door, but increasingly, your ability to navigate everything that happens afterwards matters.
And that’s where autonomy starts becoming really important.
We’re not just human robots anymore
One of the legacies of the Industrial Age was the ability to narrow work down. Define the task, define the process, train somebody to perform it, then create consistency around the result.
That was incredibly powerful.
Digital work is different.
Increasingly, we need people to understand what they’re doing, why they’re doing it and what else it connects to. We need people to make decisions, exercise judgement, move between ideas and solve problems that don’t necessarily have a documented answer waiting for them.
We need autonomy because the human being doing the work increasingly needs to bring themselves to it.
And that’s a profound change.
It means those narrow silos of thinking we’ve been so comfortable with start becoming less useful too. The person who understands only their little part of the machine can become less valuable than the person who understands their part and sees how it connects to everything around it.
The boundaries then start disappearing as well.
Work doesn’t always stay at work anymore because the problem doesn’t politely disappear from your brain at 5pm. Sometimes you’re doing something completely unrelated and the answer appears. Sometimes an idea turns up in the middle of the night. Sometimes the thing you’ve been trying to solve for three days suddenly makes sense while you’re doing something else entirely. That can be an incredibly powerful way of tackling deep human work, because focus and problem-solving don’t always happen on command.
That doesn’t mean we shouldn’t have boundaries. Bloody hell, some of us need them more than most.
But it does mean the relationship has changed.
Work, home, creativity, relationships, learning, interests and the rest of our lives don’t necessarily sit inside neat little boxes anymore. Ideas flow between them. Skills flow between them. Inspiration flows between them. Who we are flows between them.
And for a lot of neuro-complex people reading this, there’s probably something rather familiar about that.
I was having this crisis in my 20s
Looking backwards, I can see a version of this playing out in my own life long before I had any idea what neurodivergence had to do with me.
In my early 20s, back in the early 2000s, I was following the prescription too. Get qualified. Have the career. Meet girls. Date. Find somebody. Get married. Build a life. Do all those things that seemed to be part of becoming a successful adult.
The career side worked incredibly well.
My natural detail-oriented approach to the world found a home in technology. I could disappear deeply into systems and understand them. I could see connections. I could pull things apart, work out how they functioned and solve problems. I could see how all of that connected into business systems, analytics, economics and, eventually, how the world itself works. You can always trust a polymath to start connecting things that apparently weren’t supposed to belong together. The technology industry rewarded parts of the way my brain naturally worked.
Then I’d step outside that world and wonder what the hell happened.
Relationships didn’t work the same way. Dating certainly didn’t. Meeting people, communicating and connecting outside that technical sphere could be enormously difficult. I could be incredibly capable in one part of my life and then find myself completely unable to understand why something that seemed so straightforward for somebody else required so much effort from me.
And it was exhausting. I didn’t know I was autistic. I didn’t know I had ADHD. I didn’t know I was a functional polymath.
I didn’t know that the experience I was having of the world could be fundamentally different from somebody else’s. What I was experiencing was normal to me; I never thought that it would be so different an experience from others.
I just knew that I seemed to be very good at being Mike in some places and apparently rather terrible at being the version of Mike I thought I was supposed to be everywhere else.
It would take a long while before some of that finally made sense.
Looking back now, I can recognise the neurodivergent Mike in his early 20s trying to follow a prescription that didn’t really account for the way he experienced the world.
Which brings us back to the Millennial Career Crisis.
Because suddenly a lot more people are discovering that the prescription doesn’t account for the world they’re living in either.
Not for the same reason and that’s important.
But there is a remarkably familiar tension underneath it.
What happens when conformity stops being rewarded?
For generations, conformity could be a perfectly rational strategy.
Follow the path. Learn the process. Do the job. Build the career. Progress through the hierarchy.
But look at what the digital world increasingly asks of us.
We need to navigate change. We need to solve problems. We need autonomy. We need to learn things that didn’t exist when we became qualified. We need to move between ideas and sometimes between entire careers. We need to operate in situations where nobody has the answer yet. We need to connect things that don’t obviously belong together.
We need creativity.
And I don’t just mean painting a picture or masterpiece, writing a song or doing something else we traditionally label as creative.
Creativity can be deeply technical.
Looking at a system and seeing another way of building it is creative. Connecting two ideas from completely different places is creative. Asking why everybody does something a particular way and then imagining another way is creative. Seeing a problem nobody else has noticed yet is creative. Going so deeply into something that you start finding connections nobody standing on the surface could see is creative.
That is artistic expression too.
It just doesn’t necessarily involve a paintbrush.
Notice a theme here?
Because an awful lot of the things we’re increasingly going to need in this world are things neuro-complex people can be extraordinarily good at.
And I want to be really deliberate about saying that.
This isn’t another neurodivergent superpower story.
I’m not saying neuro-complex people are superior. I’m not saying every autistic person is a systems genius, every ADHD person is wildly creative, or that neurotypical people can’t do any of these things.
Of course they can.
I’m saying something to the people who’ve spent years being told that the way their brain works is somehow inconvenient.
Look at what you can do.
That detail.
That curiosity.
That ability to go incredibly deep.
That questioning.
That ability to connect seemingly unrelated things.
That creative expression.
That out-of-the-box way of looking at something everybody else accepted as obvious.
That capacity to find another way when the expected way doesn’t fit.
We need those things.
Perhaps more than we have for a very long time.
Maybe we’ve been getting ready for this
In the last article I asked where the hell all these neurodivergent people have been.
Maybe there’s another way of looking at the answer.
Perhaps some of them have spent decades learning how to operate when the obvious path doesn’t quite work.
They found the technical department where their brain made sense. They found the workshop. The art room. The shed. The club. The small business. The interest that became a career. The career that became three different things. The thing they became incredibly good at because somebody finally stopped telling them how they were supposed to do it and gave them enough room to work it out themselves.
They learnt how to find another way.
Not because that experience was always wonderful.
It wasn’t.
And not because neuro-complex people are somehow naturally invincible or endlessly resilient. We’re not. But bloody hell, you might surprise yourself at just how resilient and adaptable you can be when you’re finally allowed to operate in a way that works for you.
When the standard path hasn’t quite fitted you for most of your life, finding another path becomes something you’re rather familiar with.
Now look at the world around us.
The standard path is starting to fit far fewer people.
So no, people experiencing the Millennial Career Crisis aren’t all neurodivergent.
That’s not the point.
Perhaps they’re experiencing, from a completely different starting point, something neuro-complex people have known for a very long time.
The strange moment when you realise doing what you were told doesn’t necessarily get you where you thought it would.
And then having to ask:
What now?
And what a bloody time for that question
Because we’re not simply changing careers.
We’re standing in this strange place where the old Industrial Age and the digital age are butting heads.
The Industrial Age gave us incredible capability to scale. To manufacture. To organise. To standardise. To produce more and distribute further.
Digital has taken that capability and turned the dial so far that sometimes it feels like we’ve snapped the bloody thing off.
We can make almost anything.
We can publish almost anything.
We can reach almost anybody.
We can automate things that would have seemed impossible not that long ago.
And now AI has arrived and suddenly we can generate more again.
More words. More images. More video. More code. More information. More everything.
We’re already talking about AI slop because we have discovered that the ability to create enormous quantities of something doesn’t magically mean any of it is worth having.
But look around. That’s not just an AI problem.
Go onto eBay, AliExpress or Alibaba and look at what our global manufacturing capability has made possible. Somewhere, somebody can make almost anything for anybody.
That’s extraordinary.
But how much of it is actually any good?
How much of it did we need?
How much gets manufactured from materials, packaged, transported halfway around the world, used briefly and thrown away?
We see another version of this tension in property and speculative markets, where the numbers attached to an asset can increasingly feel disconnected from the value experienced by the person simply trying to have somewhere to live.
We have become extraordinarily capable of creating, scaling, manufacturing and extracting value.
Is this the “enshittification” of, well… everything? Not just the internet?
Moving on… capability alone doesn’t tell us whether we’re doing a good job.
That’s where these two worlds start butting heads.
Because perhaps the question ahead of us isn’t simply whether we can do something.
It’s whether we should.
And suddenly we’re not talking about careers anymore.
We’re talking about leadership.
We need great thinking now
This is where I get excited.
Because we need great thinking in this world.
We need great influence.
We need great leadership.
We need people who can look at all this extraordinary capability and ask what we’re actually trying to achieve with it. Great leaders wrestle with the big issues. They look beyond the immediate gain towards the end goal and ask what the right and good thing actually is. They’re strategic, but they also bring what it is to be human into that strategy. Because when our capability to make, automate, scale, influence and extract becomes almost unlimited, leadership isn’t just about figuring out how to do more of it. Leadership is having the judgement to know when we should, when we shouldn’t, and what we’re actually trying to create in the first place.
We need people willing to question things.
We need people who can connect consequences that don’t sit neatly together.
We need people prepared to say no when everybody else is excited about saying yes.
We need people who can imagine another way.
We need people who can see something that doesn’t exist yet and start bringing it to life.
And what better moment for neuro-complex people to recognise that they have a place in this?
That sense of justice that can be so incredibly powerful.
That curiosity.
That depth.
Those ideas.
Those connections.
That ability to question something simply because it doesn’t make sense, even when everybody else has apparently agreed to stop asking.
That creative capability that doesn’t always look like creativity.
That different way of seeing.
For years some of those things have been the reason people were pushed aside.
- Too direct.
- Too intense.
- Too much.
- Not enough executive presence.
- Not leadership material.
- Keep them technical.
- Let them do their thing over there.
And now?
Bloody hell.
Look at what the world needs.
I want neurocomplex people to understand that.
Not because you’re better than everybody else.
Because you’re capable.
Far more capable than many of you have probably been encouraged to believe.
And the world we’re moving into has room for that capability in places the old one often didn’t.
Different doesn’t mean the same
There’s an important caution in all of this though. The tension might increasingly be shared, but the experience isn’t the same.
If neurotypical people are beginning to experience some of the same tension with the old playbook, that doesn’t mean they’re suddenly experiencing neurodivergence.
They’re not the same thing.
We seem to be living through a period where there’s a temptation to label everything, and then somehow flatten everybody back together underneath the labels.
We’re all different.
Actually different.
For a lot of autistic and other neurodivergent people, particularly those whose disability isn’t immediately visible from the outside, what you see isn’t necessarily what they experience.
You might see somebody going to work, running a business, having relationships, doing their hobbies, talking to people and apparently getting along perfectly well.
You don’t see everything happening underneath.
- You don’t see the energy.
- The processing.
- The emotions.
- The nervous system.
- The brain that feels like it’s running and running and running.
You don’t necessarily see the cost of getting through an environment that somebody else barely notices.
So we need to recognise the similarities in the tensions we’re experiencing without pretending our experiences are identical.
And That’s important.
Because this isn’t about making everybody the same.
It’s about becoming much better at understanding people who aren’t.
Clarity is kindness
This is why I keep coming back to communication.
I say clarity is kindness because it really is.
When I ask why, I’m not necessarily challenging you.
I’m building understanding.
And there is something beyond what we normally describe as active listening that I reckon matters enormously here.
Listening to build understanding.
Because communication between two people can be a translation exercise even when they’re both speaking English. Say that again…. even when they’re both speaking English.
I can say something and know exactly what I mean. You can hear exactly the same words and understand something completely different.
Neither of us necessarily did anything wrong.
We translated it differently.
Listening to build understanding means being willing to stop there and work it out.
- What did you mean?
- What did I hear?
- Why did I interpret it that way?
- What did you hear when I said this?
- What am I missing?
That’s not merely repeating somebody’s words back to them to prove we’ve been listening. It’s doing the work required to understand another human being through many different routes.
And it goes both ways.
This isn’t neurotypical people having a responsibility to learn the mysterious language of neuro-complex people. Neurocomplex people need to understand that other people experience and communicate differently too.
So, WE ALL have a responsibility here.
Because if we’re serious about building a world that can make use of all these different ways of thinking, we have to be able to understand each other well enough to actually work together.
Maybe this isn’t a crisis
So perhaps we need to look at the Millennial Career Crisis slightly differently.
Yes, there are people in their 30s, 40s and beyond looking around at the career and life they built and wondering why it doesn’t look the way they expected.
Yes, the prescription changed.
Yes, the boundaries between work, home, identity, creativity and purpose aren’t as clear as they once seemed to be.
And yes, that can be incredibly uncomfortable.
But some of these people are also rediscovering themselves.
They’re starting again.
They’re finding things they had forgotten about.
They’re realising that the career they chose at 20 doesn’t have to define the person they are at 40. That’s wonderful, scary and can be fun too.
Maybe that’s what it feels like when the old playbook stops working, and we finally give ourselves permission to write another one.
And for the neuro-complex people amongst us, perhaps there’s an even bigger invitation sitting inside that.
You’ve already spent a lifetime learning that the obvious path isn’t always your path.
You’ve already had to think differently.
You’ve already found your places.
You’ve already built things around the way your brain works, sometimes without even realising that’s what you were doing.
Now we are moving into a world that desperately needs people who can imagine what comes next.
Leadership is about being able to see that future, resource it, enable it and bring it to life.
You can do that.
Neuro-complex people can lead.
Pssst… and we can do it without drama, manipulation, coercion, misrepresentation or toxicity.
We can create, influence, build, challenge and connect. We can take all those strange and wonderful ways our brains work and use them to shape something that doesn’t exist yet.
We’re at this Catalyst moment between two worlds, with one playbook losing its grip and another one still being written.
We don’t need everybody to think the same way anymore.
We need to get much better at understanding what happens when they don’t.
Perhaps it’s a whole generation beginning to realise that the future was never going to look like the prescription they were handed.
For some of us, that’s not a new feeling.
We’ve been getting ready for this for a very long time.
